Bis(tetra­phenyl­phospho­nium) tetra­chlorido­cobaltate(II)

Ouahida, Z.; Hadjadj, N.; Guenifa, F.; Bendjeddou, L.; Merazig, H.

doi:10.1107/S1600536814011210

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Pages m229-m230

doi:10.1107/S1600536814011210

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Bis(tetraphenylphosphonium) tetrachloridocobaltate(II)

Zeghouan Ouahida,^a Nasreddine Hadjadj,^a Fatiha Guenifa,^a Lamia Bendjeddou ^a ^* and Hocine Merazig ^a

^aUnité de Recherche Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Campus Chaabet Ersas, Université Constantine I, 25000 Constantine, Algeria
^*Correspondence e-mail: Lamia_bendjeddou@yahoo.fr

(Received 7 May 2014; accepted 15 May 2014; online 21 May 2014)

The title compound, (C₂₄H₂₀P)₂[CoCl₄], was prepared under hydrothermal conditions. In the crystal, the tetraphenylphosphonium cations are linked by pairs of weak C—H⋯π interactions into supramolecular dimers; the Co^II cations lie on twofold rotation axes and the tetrahedral [CoCl₄]²⁻ anions are linked with the tetraphenylphosphonium cations via weak C—H⋯Cl hydrogen bonds.

CCDC reference: 1003287

Related literature

For background and applications of compounds with supramolecular structures, see: Rowsell & Yaghi (2005 ); Dong et al. (2007 ); Wu & Lin (2007 ); Zhao et al. (2003 ); Neville et al. (2008 ); Huang et al. (2007 ). For applications of the tetraphenylphosphonium ion in supramolecular chemistry and numerous coordination polymers, see: Zacharie et al. (1985 ); Schlueter & Geiser (2007 ).

Experimental

Crystal data

(C₂₄H₂₀P)₂[CoCl₄]
M_r = 879.46
Monoclinic, C 2/c
a = 10.9154 (4) Å
b = 19.2514 (6) Å
c = 20.1826 (7) Å
β = 91.008 (2)°
V = 4240.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.77 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.08 mm

Data collection

Bruker APEXII diffractometer
12226 measured reflections
3748 independent reflections
3180 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.084
S = 1.04
3748 reflections
249 parameters
H-atom parameters constrained
Δρ_max = 1.51 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—Cl2	2.2791 (6)
Co1—Cl1	2.2873 (6)

Table 2
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the C19–C24 and C7-C12 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cl1	0.93	2.80	3.552 (3)	138
C11—H11⋯Cl1ⁱ	0.93	2.81	3.633 (2)	148
C23—H23⋯Cl2ⁱⁱ	0.93	2.77	3.644 (2)	156
C14—H14⋯Cg4ⁱⁱⁱ	0.93	2.88	3.650 (2)	141
C21—H21⋯Cg2ⁱⁱⁱ	0.93	2.79	3.446 (2)	129
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012), Mercury (Macrae et al., 2006 ) and POVRay (Persistence of Vision Team, 2004 ).

Supporting information

CCDC reference: 1003287

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814011210/xu5791sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814011210/xu5791Isup2.hkl

checkCIF report

Comment top

Research on supramolecular compounds has become popular because of their potential applications in areas such as gas storage (Rowsell & Yaghi, 2005), selective absorption (Dong et al., 2007), catalysis (Wu & Lin, 2007), magnetics (Zhao et al., 2003; Neville et al., 2008) and optics (Huang et al., 2007). P-Ligands are important structural motifs in organic syntheses, coordination chemistry and also in various catalytically active compounds, the tetraphenylphosphonium ion have been widely used in supramolecular chemistry and numerous coordination polymers with versatile structures and potential properties have been reported (Zacharie et al., 1985; Schlueter & Geiser, 2007). Thus, we report here the synthesis of title compound [L₂.CoCl₄], were L is tetraphenylphosphonium and its crystal structure.

The asymmetric unit of (I) and atomic numbering are illustrated in Fig. 1. The (I) contains tetraphenylphosphonium cations linked by weak C—H···π supramolecular interactions into dimmers. The Co^II ion lies on a twofold axis and has a distorted tetrahedral coordination. The [CoCl₄]^-2 anions are linked with the cation via weak C—H···Cl hydrogen bonds (Fig. 2, 3).

The bond lengths for coordination Co^II sphere is ranging from 2.2791 (6) to 2.2873 (6) Å for Co—Cl distances (Table 1). The crystal packing in the title structure can be described by altering CoCl₄ tetrahedral of complex along the a axis at b = 1/4 and 3/4 (Fig. 2).

Related literature top

For background and potential applications of supramolecular compounds, see: Rowsell & Yaghi (2005); Dong et al. (2007); Wu & Lin (2007); Zhao et al. (2003); Neville et al. (2008); Huang et al. (2007). For applications of the tetraphenylphosphonium ion in supramolecular chemistry and numerous coordination polymers, see: Zacharie et al. (1985); Schlueter & Geiser (2007).

Experimental top

A mixture of CoCl₂ (2.50 g, 10 mmol), tetraphenylphosphonium chloride hydrate (3.92 g,10 mmol) was dissolved in a 20 ml EtOH/H₂O(v/v,1:2). The mixture was then sealed in a 25 ml stainless steel reactor and heated to 433 K for 3 days. Then the reactant mixture was cooled to room temperature at the rate of 5 degrees per hour. Evaporation of the resulting solution for a few days afforded pink crystals of title compound.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012), Mercury (Macrae et al., 2006) and POVRay (Persistence of Vision Team, 2004).

Figures top

	Fig. 1. The asymmetric unit of the title structure with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (*): -x, y, 1/2 - z].
	Fig. 2. Part of the layered packing in the crystal viewed down the b axis.
	Fig. 3. A view along the c axis of the crystal structure of the title compound, showing C—H···Cl hydrogen-bonds.

Bis(tetraphenylphosphonium) tetrachloridocobaltate(II) top

Crystal data top

(C₂₄H₂₀P)₂[CoCl₄]	F(000) = 1812
M_r = 879.46	D_x = 1.378 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1536 reflections
a = 10.9154 (4) Å	θ = 3.2–25.1°
b = 19.2514 (6) Å	µ = 0.77 mm⁻¹
c = 20.1826 (7) Å	T = 293 K
β = 91.008 (2)°	Prism, pink
V = 4240.4 (3) Å³	0.2 × 0.1 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	3180 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 25.1°, θ_min = 2.0°
ϕ scans	h = −12→12
12226 measured reflections	k = −22→22
3748 independent reflections	l = −24→22

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.030	w = 1/[σ²(F_o²) + (0.0401P)² + 6.1572P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.084	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 1.51 e Å⁻³
3748 reflections	Δρ_min = −0.22 e Å⁻³
249 parameters

Crystal data top

(C₂₄H₂₀P)₂[CoCl₄]	V = 4240.4 (3) Å³
M_r = 879.46	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 10.9154 (4) Å	µ = 0.77 mm⁻¹
b = 19.2514 (6) Å	T = 293 K
c = 20.1826 (7) Å	0.2 × 0.1 × 0.08 mm
β = 91.008 (2)°

Data collection top

Bruker APEXII diffractometer	3180 reflections with I > 2σ(I)
12226 measured reflections	R_int = 0.028
3748 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.04	Δρ_max = 1.51 e Å⁻³
3748 reflections	Δρ_min = −0.22 e Å⁻³
249 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
P1	0.41273 (5)	0.36748 (3)	0.07765 (3)	0.0200 (2)
C1	0.3837 (2)	0.29974 (11)	0.13639 (11)	0.0233 (7)
C2	0.3155 (2)	0.31597 (12)	0.19182 (11)	0.0308 (7)
C3	0.2894 (3)	0.26481 (13)	0.23755 (13)	0.0376 (8)
C4	0.3336 (2)	0.19823 (12)	0.22924 (12)	0.0355 (8)
C5	0.4026 (2)	0.18228 (12)	0.17495 (12)	0.0335 (8)
C6	0.4272 (2)	0.23227 (11)	0.12800 (12)	0.0290 (7)
C7	0.5226 (2)	0.33873 (11)	0.01785 (11)	0.0238 (7)
C8	0.6408 (2)	0.36542 (13)	0.01635 (12)	0.0291 (7)
C9	0.7214 (2)	0.34138 (14)	−0.03052 (13)	0.0375 (8)
C10	0.6855 (2)	0.29065 (13)	−0.07487 (12)	0.0370 (8)
C11	0.5686 (3)	0.26452 (12)	−0.07432 (12)	0.0363 (8)
C12	0.4866 (2)	0.28862 (12)	−0.02847 (12)	0.0314 (7)
C13	0.27533 (19)	0.39129 (10)	0.03328 (10)	0.0199 (6)
C14	0.2858 (2)	0.42599 (12)	−0.02717 (11)	0.0272 (7)
C15	0.1824 (2)	0.44748 (12)	−0.06129 (11)	0.0297 (7)
C16	0.0676 (2)	0.43485 (12)	−0.03560 (11)	0.0269 (7)
C17	0.0570 (2)	0.40171 (12)	0.02446 (11)	0.0271 (7)
C18	0.1604 (2)	0.38005 (11)	0.05921 (11)	0.0232 (7)
C19	0.47179 (19)	0.44088 (11)	0.12202 (10)	0.0205 (6)
C20	0.4177 (2)	0.50598 (11)	0.11488 (11)	0.0226 (6)
C21	0.4699 (2)	0.56215 (12)	0.14713 (11)	0.0289 (7)
C22	0.5746 (2)	0.55408 (13)	0.18543 (11)	0.0304 (7)
C23	0.6265 (2)	0.48956 (14)	0.19401 (11)	0.0315 (8)
C24	0.5750 (2)	0.43278 (13)	0.16272 (11)	0.0280 (7)
Co1	0.00000	0.45721 (2)	0.25000	0.0202 (1)
Cl1	0.10790 (5)	0.38813 (3)	0.32242 (3)	0.0338 (2)
Cl2	0.12506 (5)	0.52482 (3)	0.18779 (3)	0.0267 (2)
H2	0.28760	0.36110	0.19810	0.0370*
H3	0.24190	0.27530	0.27400	0.0450*
H4	0.31670	0.16410	0.26040	0.0430*
H5	0.43290	0.13750	0.16980	0.0400*
H6	0.47250	0.22100	0.09090	0.0350*
H8	0.66550	0.39920	0.04670	0.0350*
H9	0.80030	0.35960	−0.03210	0.0450*
H10	0.74100	0.27400	−0.10550	0.0440*
H11	0.54480	0.23060	−0.10480	0.0440*
H12	0.40700	0.27140	−0.02840	0.0380*
H14	0.36280	0.43460	−0.04440	0.0330*
H15	0.18950	0.47050	−0.10160	0.0360*
H16	−0.00230	0.44880	−0.05900	0.0320*
H17	−0.02010	0.39380	0.04180	0.0330*
H18	0.15280	0.35800	0.09990	0.0280*
H20	0.34740	0.51150	0.08870	0.0270*
H21	0.43410	0.60580	0.14300	0.0350*
H22	0.61050	0.59260	0.20570	0.0360*
H23	0.69600	0.48430	0.22080	0.0380*
H24	0.60930	0.38900	0.16880	0.0340*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0206 (3)	0.0189 (3)	0.0205 (3)	0.0001 (2)	0.0001 (2)	−0.0013 (2)
C1	0.0266 (12)	0.0210 (11)	0.0222 (11)	−0.0004 (9)	−0.0037 (9)	0.0011 (9)
C2	0.0441 (14)	0.0228 (12)	0.0255 (12)	0.0057 (11)	0.0025 (11)	0.0007 (9)
C3	0.0528 (16)	0.0346 (14)	0.0256 (13)	0.0020 (12)	0.0065 (12)	0.0037 (11)
C4	0.0484 (15)	0.0275 (13)	0.0303 (13)	−0.0040 (11)	−0.0064 (12)	0.0096 (10)
C5	0.0454 (15)	0.0187 (11)	0.0361 (14)	0.0038 (11)	−0.0070 (12)	0.0010 (10)
C6	0.0324 (13)	0.0255 (12)	0.0291 (12)	0.0037 (10)	−0.0013 (10)	−0.0025 (10)
C7	0.0272 (12)	0.0207 (11)	0.0235 (11)	0.0042 (9)	0.0018 (9)	0.0013 (9)
C8	0.0240 (12)	0.0355 (13)	0.0279 (12)	0.0022 (10)	−0.0009 (10)	0.0005 (10)
C9	0.0236 (12)	0.0548 (16)	0.0343 (14)	0.0069 (12)	0.0030 (11)	0.0031 (12)
C10	0.0404 (15)	0.0422 (15)	0.0286 (13)	0.0170 (12)	0.0101 (11)	0.0036 (11)
C11	0.0554 (17)	0.0254 (12)	0.0284 (13)	0.0060 (12)	0.0080 (12)	−0.0034 (10)
C12	0.0372 (13)	0.0252 (12)	0.0319 (13)	−0.0035 (10)	0.0056 (11)	−0.0036 (10)
C13	0.0212 (11)	0.0186 (10)	0.0199 (11)	−0.0011 (9)	−0.0018 (9)	−0.0027 (8)
C14	0.0239 (12)	0.0340 (13)	0.0237 (12)	−0.0033 (10)	0.0031 (9)	0.0040 (10)
C15	0.0342 (13)	0.0345 (13)	0.0203 (11)	−0.0004 (11)	0.0002 (10)	0.0061 (10)
C16	0.0260 (12)	0.0286 (12)	0.0258 (12)	0.0038 (10)	−0.0048 (10)	−0.0033 (10)
C17	0.0216 (11)	0.0317 (12)	0.0282 (12)	−0.0009 (10)	0.0035 (9)	−0.0010 (10)
C18	0.0256 (12)	0.0248 (11)	0.0192 (11)	−0.0028 (9)	0.0024 (9)	0.0018 (9)
C19	0.0200 (11)	0.0219 (11)	0.0198 (11)	−0.0015 (9)	0.0036 (9)	−0.0025 (9)
C20	0.0238 (11)	0.0233 (11)	0.0208 (11)	−0.0014 (9)	0.0035 (9)	0.0007 (9)
C21	0.0395 (14)	0.0207 (11)	0.0268 (12)	−0.0033 (10)	0.0079 (11)	−0.0002 (9)
C22	0.0354 (13)	0.0335 (13)	0.0225 (12)	−0.0165 (11)	0.0072 (10)	−0.0080 (10)
C23	0.0228 (12)	0.0483 (15)	0.0235 (12)	−0.0042 (11)	−0.0001 (10)	−0.0070 (11)
C24	0.0253 (12)	0.0324 (13)	0.0262 (12)	0.0054 (10)	−0.0016 (10)	−0.0036 (10)
Co1	0.0188 (2)	0.0189 (2)	0.0231 (2)	0.0000	0.0029 (2)	0.0000
Cl1	0.0315 (3)	0.0335 (3)	0.0367 (3)	0.0084 (3)	0.0074 (3)	0.0151 (3)
Cl2	0.0234 (3)	0.0296 (3)	0.0270 (3)	−0.0035 (2)	0.0015 (2)	0.0071 (2)

Geometric parameters (Å, º) top

Co1—Cl2	2.2791 (6)	C19—C24	1.391 (3)
Co1—Cl1ⁱ	2.2873 (6)	C19—C20	1.392 (3)
Co1—Cl1	2.2873 (6)	C20—C21	1.380 (3)
Co1—Cl2ⁱ	2.2791 (6)	C21—C22	1.377 (3)
P1—C1	1.794 (2)	C22—C23	1.375 (4)
P1—C7	1.803 (2)	C23—C24	1.377 (3)
P1—C13	1.793 (2)	C2—H2	0.9301
P1—C19	1.787 (2)	C3—H3	0.9296
C1—C6	1.394 (3)	C4—H4	0.9302
C1—C2	1.390 (3)	C5—H5	0.9298
C2—C3	1.383 (3)	C6—H6	0.9302
C3—C4	1.381 (3)	C8—H8	0.9301
C4—C5	1.375 (3)	C9—H9	0.9310
C5—C6	1.380 (3)	C10—H10	0.9301
C7—C8	1.390 (3)	C11—H11	0.9310
C7—C12	1.395 (3)	C12—H12	0.9300
C8—C9	1.383 (3)	C14—H14	0.9301
C9—C10	1.377 (4)	C15—H15	0.9309
C10—C11	1.372 (4)	C16—H16	0.9299
C11—C12	1.379 (4)	C17—H17	0.9297
C13—C14	1.397 (3)	C18—H18	0.9295
C13—C18	1.385 (3)	C20—H20	0.9301
C14—C15	1.375 (3)	C21—H21	0.9299
C15—C16	1.386 (3)	C22—H22	0.9302
C16—C17	1.376 (3)	C23—H23	0.9293
C17—C18	1.383 (3)	C24—H24	0.9295

Cl1—Co1—Cl2	112.17 (2)	C22—C23—C24	119.7 (2)
Cl1—Co1—Cl1ⁱ	108.90 (3)	C19—C24—C23	120.1 (2)
Cl1—Co1—Cl2ⁱ	106.66 (2)	C3—C2—H2	120.17
Cl1ⁱ—Co1—Cl2	106.66 (2)	C1—C2—H2	120.06
Cl2—Co1—Cl2ⁱ	110.35 (3)	C2—C3—H3	119.85
Cl1ⁱ—Co1—Cl2ⁱ	112.17 (2)	C4—C3—H3	119.91
C13—P1—C19	109.84 (10)	C3—C4—H4	119.98
C1—P1—C19	108.05 (10)	C5—C4—H4	119.92
C1—P1—C7	110.27 (10)	C6—C5—H5	119.72
C1—P1—C13	111.10 (10)	C4—C5—H5	119.80
C7—P1—C13	107.73 (10)	C1—C6—H6	120.13
C7—P1—C19	109.86 (10)	C5—C6—H6	120.17
P1—C1—C6	122.16 (17)	C7—C8—H8	120.18
P1—C1—C2	118.14 (17)	C9—C8—H8	120.26
C2—C1—C6	119.7 (2)	C10—C9—H9	119.85
C1—C2—C3	119.8 (2)	C8—C9—H9	119.83
C2—C3—C4	120.2 (2)	C9—C10—H10	119.68
C3—C4—C5	120.1 (2)	C11—C10—H10	119.72
C4—C5—C6	120.5 (2)	C12—C11—H11	120.17
C1—C6—C5	119.7 (2)	C10—C11—H11	120.04
P1—C7—C8	121.99 (17)	C7—C12—H12	119.84
P1—C7—C12	118.55 (17)	C11—C12—H12	119.90
C8—C7—C12	119.5 (2)	C13—C14—H14	120.00
C7—C8—C9	119.6 (2)	C15—C14—H14	119.88
C8—C9—C10	120.3 (2)	C16—C15—H15	120.01
C9—C10—C11	120.6 (2)	C14—C15—H15	120.04
C10—C11—C12	119.8 (2)	C15—C16—H16	119.90
C7—C12—C11	120.3 (2)	C17—C16—H16	120.01
C14—C13—C18	119.55 (19)	C16—C17—H17	119.87
P1—C13—C18	121.79 (16)	C18—C17—H17	119.73
P1—C13—C14	118.54 (16)	C17—C18—H18	120.08
C13—C14—C15	120.1 (2)	C13—C18—H18	120.05
C14—C15—C16	120.0 (2)	C19—C20—H20	120.40
C15—C16—C17	120.1 (2)	C21—C20—H20	120.54
C16—C17—C18	120.4 (2)	C20—C21—H21	119.77
C13—C18—C17	119.9 (2)	C22—C21—H21	119.71
P1—C19—C24	119.24 (17)	C23—C22—H22	119.70
P1—C19—C20	120.76 (16)	C21—C22—H22	119.73
C20—C19—C24	120.0 (2)	C22—C23—H23	120.14
C19—C20—C21	119.1 (2)	C24—C23—H23	120.18
C20—C21—C22	120.5 (2)	C23—C24—H24	119.93
C21—C22—C23	120.6 (2)	C19—C24—H24	119.98

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of the C19–C24 and C7-C12 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl1	0.93	2.80	3.552 (3)	138
C11—H11···Cl1ⁱⁱ	0.93	2.81	3.633 (2)	148
C23—H23···Cl2ⁱⁱⁱ	0.93	2.77	3.644 (2)	156
C14—H14···Cg4^iv	0.93	2.88	3.650 (2)	141
C21—H21···Cg2^iv	0.93	2.79	3.446 (2)	129

Symmetry codes: (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+1, y, −z+1/2; (iv) −x+1, −y+1, −z.

Selected bond lengths (Å) top

Co1—Cl2

2.2791 (6)

Co1—Cl1

2.2873 (6)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of the C19–C24 and C7-C12 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl1	0.93	2.80	3.552 (3)	138
C11—H11···Cl1ⁱ	0.93	2.81	3.633 (2)	148
C23—H23···Cl2ⁱⁱ	0.93	2.77	3.644 (2)	156
C14—H14···Cg4ⁱⁱⁱ	0.93	2.88	3.650 (2)	141
C21—H21···Cg2ⁱⁱⁱ	0.93	2.79	3.446 (2)	129

Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) −x+1, y, −z+1/2; (iii) −x+1, −y+1, −z.

Acknowledgements

This work was supported by the Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Université de Constantine 1, Algeria. Thanks are due to MESRS and ATRST (Ministère de l'Enseignement Supérieur et de la Recherche Scientifique et l'Agence Thématique de Recherche en Sciences et Technologie, Algérie) for financial support via the PNR program.

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Volume 70| Part 6| June 2014| Pages m229-m230

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